Warning! This story is sexually explicit, so, if you are not of legal age to read such or are offended by this type of writing do not read any further. If you would care to read more contact the author. To contact the author cut and paste making appropriate corrections and E-mail: bn2rumpranger "at" yahoo "dot" com
The First Time I Was Digitally Diddled
By Randy Rumper
The first time I discovered the thrill of being finger fucked up my ass by another guy I screamed out, wailing in pure ecstasy. Oh My God, what an incredible experience that first time was as Bobby dexterously diddled me with his middle digit. Bobby BoDiddly had beautiful hands and feet; his hands and feet were what made me take notice of him. The first time we met and shook hands I was taken by the beauty of his long slender fingers with finger nails so well manicured. I would discover months later that those fingers were very adept at the art of digital diddling.
Bobby and I were unlikely roommates. He was not a particularly good-looking guy, nor was he well endowed. Bobby wasn't blessed with bulging biceps, powerful pecs or well-defined abdominal muscles. His physical characteristics were that of the typical gangling geek; whereas, I was the athlete with a strong body and good looks. My nerdy roommate was a quiet bookworm who never ventured out to participate in extracurricular actives; whereas, I was the social butterfly. Despite our differences Bobby and I had grown very close over the course of that first semester. We spent many nights confiding in each other our deepest intimacies and secrets. As the first semester was drawing to a close we decided to pool our resources and spend the break between semesters together on the coast of Florida instead of going home.
For Bobby and me, two eighteen year old collegiate freshmen, living away from home for the first time in our lives was a new and enlightening experience. At almost nineteen I was somewhat of a naive neophyte when it came to sex and sexuality; however, living with my roommate was fast becoming an edifying experience. A roommate who would educate me in the ways male-on-male lovemaking; needless to say, I was thrilled when I discovered that my roomy was a homosexual. I was not sure who or what I was yet, but I knew instinctively that my roomy would help me discover my niche in life -- my own sexuality.
My place in life and my sexual lifestyle had been in turmoil for years. I had a girlfriend who I had dated for two years in high school; however, she was now attending another college over a thousand miles away. I wanted to do the nasty with her during our relationship, but all she would do was fist fuck me. She attempted to give me blow jobs on a couple occasions, but she just didn't understand nor could she master the mechanics of how to do it. She gagged, spit and even hurled on one occasion. My sister's girlfriend's cousin however had performed oral sex on me a few times the summer between my junior and senior year in high school. She was good at it and I couldn't get enough. That had been the extent of my sexual involvement thus far in life. My sexual lifestyle had not yet been defined; however, I was sure that Bobby was going to be the one who would help me map out my future.
I knew from that first blowjob that I was hooked on oral sex. I also knew after the first time I'd touched another guy's dick that I wanted to experiment sexually with other males. Mid way through our first semester Bobby and I rented a cottage on the Gulf coast of Florida for the break between semesters. We planned to spend our break getting more intimately acquainted. During the first semester in college Bobby and I had discussed sex, but had yet to do anything other than mutual masturbation on a couple occasions.
One night before we took off for our break between semesters, we sat across the table from each other drinking wine and talking about sex well into the night. After a bottle of wine I'd become a little amorous in my inebriated state, so I reached across the table and took one of Bobby's hands into mine. As my fingers explored his hand I stroked and admired his fingers, telling him what great looking hands he had. I remember telling Bobby that I would enjoy having him explore my anal cavity with his delightful looking middle digit. He replied that he would enjoy doing me with it. He asked me if I had ever been diddled or cornholed before. To which I replied, no. He told me he wanted to change that very soon. I asked him why we didn't try it that night. To which he responded only when the time is right.
Bobby had asked me during our conversations about my sexual experiences thus far in my life. I told him that my sex life had been limited, but now that I was free of parental control I wanted to expand my wings and fly. I went on telling him how I played with my asshole a few times when I was younger and what an exhilarating feel it produced. I told him how I would wet my middle finger with saliva or baby oil, playing around rubbing the entrance to my asshole of a night while I lay in bed jacking off. Also, when I took a bath or shower I would soap up my ass and play with my asshole. However, the few times I'd actually inserted my finger in my rectal cavity I withdrew it finding fecal matter attached as well as nasty stink of shit to my finger. So, by the time I was in high school I knew my asshole was super sensitive to touch, but also came with an offensive odor.
As we sat across from each other I told Bobby that I'd heard and read that some guys found anything penetrating their assholes to be repugnant and taboo. Others found anal sex play to be a very enjoyable and sensual experience. I informed Bobby that I thought I would enjoy anal sex, and moan out in ecstasy if he were to diddle my asshole with one of his beautiful fingers. I also told him I thought that I was one of those who would find cornholing to be very sensuous. Bobby interrupted telling me that is why he wanted to wait until we were away from the dorm before doing anything.
My roomy told me that he wanted us to be alone and free, so we might sing out gleefully as we sexual stimulated each other. I told Bobby that for me to be finger fucked while receiving a blowjob would probably be the ultimate in sexual pleasure, bringing on wanton wails of desire from me. I told him that during recess in junior high school I'd heard stories from the older boys about them finger fucking their girl friends. Of course, they always wanted to pass the odoriferous digit under our novice noses for everyone to sniff the scent of the freshly finger fucked girlfriend. I also heard stories about guy's cornholing each other. Although curious I had never indulged.
Since we'd been rooming together we would go online occasionally after classes and read stories about gay sex. We even watched gay porn on a few occasions. We would discuss these stories and flicks along with what we might engage in during the winter break. Bobby told me the first night we'd start off slow, sucking each other off and then move on. Bobby also told me that he wanted us to experiment with anal sex. He said that he had prepared and had all the bases covered. He said that it was something he had been planning for weeks prior. I had heard stories that anal sex could be painful. I didn't know first hand as I wasn't experienced in finger or butt fucking. Needless to say, I was a little apprehensive. Hell, Bobby and I had just recently engaged in our first mutual masturbation session.
Early one morning after pulling an all nighter, studying for finals, we decided to take a shower together where we begin playing with each other's stiff dicks. We spent about a half hour in the shower soaping and rubbing our hard cocks together before we ejaculated all over each other. The feeling of rubbing our cockheads together was totally exhilarating.
As we ate breakfast that morning I asked Bobby where he learned about sex with guys. He told me that his uncle who was a year older taught him. He said that he had learned everything about sex form his uncle, and he and his uncle had been playing around sexually for a while. Bobby told me that his uncle's dick was much bigger than his. He said that of course this had all been done in total secrecy. In a few days Bobby would be my sexual mentor.
As we drove towards the cottage we rented Bobby told me he and his uncle had discovered that baby oil was the best lube to use at that time; otherwise, any type anal penetration might be painful. That was my main concern -- pain. He told me it might hurt a little when he pushed his finger inside me. He also advised me to just tell him to stop and he'd wait a few seconds till I got used to it. He told me that when his uncle finger fucked him the first time he used Crisco to lube up Bobby's asshole. Bobby said that for a week after his uncle packed his ass with Crisco he shit biscuits and gravy, and then he laughed. I thought at the time how gross, using Crisco. Bobby said that since that time he had learned that there were much better lubricants on the market that were compatible with condoms.
We arrived at the cottage which was completely furnished in the late afternoon. After unpacking the car and putting our things away we took a shower together. Bobby guided me through the preparation process. He told me that prior to any anal play that cleanliness was the rule. He said the second rule was to use plenty of lubricant. We made sure our anal cavities were evacuated and cleaned. Bobby had brought all the necessary items to insure a safe and sane time. He had in his bag Fleets enemas, condoms, lubricants of different varieties. He also had brought along a couple of dildos and a vibrator. Bobby came well prepared.
We lay down on the bed opposite each other where we began playing with each other's stiffening appendages. I had never sucked a dick before, but had been sucked. Bobby told me to take my time and follow his lead. I played with his cock and balls before taking them into my mouth. Bobby was circumcised and his dick was only about four and half maybe five inches in length fully erect; it looked to be about the diameter of a "C" flashlight battery, all in all a very nice looking cock and cockhead. Size was of no concern to me; in fact, I was thankful for two things. The fact that Bobby was cut and his cock wasn't a monster.
I had read all the stories about guys swallowing cocks that were eight and ten inches long and the thickness of a beer can. I just couldn't understand how they could do that. I had tried on a couple of occasion to get my mouth around a beer or soda can. There was no way that was happening; my mouth just wasn't that big. As far as taking eight or ten inches into my mouth and all the way down my throat, that wasn't happening either. So, I was thankful my mentor wasn't overly well-endowed. Besides, I didn't think I wanted a monster cock stretching my virgin asshole, at least not as a novice.
Bobby was kissing the head of my cock; taking only the pink glans into his mouth, licking all around the head, especially the crimson coronal ring. He was taking his time exploring the full six and half inches of my manhood. His mouth and tongue were playing with my pecans inside my scrotal sac. Already I was in heaven as my mentor lavished his full oral attention on my fully aroused organ. After a few minutes of oral pleasuring Bobby pushed my legs apart and ever so gently began rubbing lubricant into my rectal area.
The first cold dollop of lube and delicate touch from his middle digit brought about a surprising sigh and then a pleasurable moan. The tip of Bobby's middle finger rubbed against my awaiting asshole but ever so delicately. He continued rubbing my pucker as he licked my cockhead. Oh My God, I was in heaven. I had to quit sucking on Bobby's dick for fear I might bite it off. I lay there waiting for the moment his finger would breach my asshole. He looked up at me and asked how I was doing. To which I had no reply, just a whimper.
I felt Bobby's finger becoming more aggressive. His finger tip began putting more pressure on my pucker. The tip of my dick was leaking. As my mentor began the penetration process his tongue found the source of leakage and was excavating precum from my piss slit. My heart was pounding and I was moaning with wanton desire. I knew then why Bobby wanted to wait until we were away from the dorm before engaging in sex. He knew how to make a grown man cry. His finger tip began pushing past the entry, the first ring. He withdrew his finger tip and applied more lubricant.
Once Bobby squeezed another dollop of lube on my back door hinges he went back to work. The lube was a little cold at first but warmed up quickly as he worked it in. Bobby would stop every once in a while to pay attention to my throbbing hard cock. Then he would move down letting his tongue titillate my taint. I waited for the point of pain as Bobby's finger penetrating my sphincter. Once he had cleared the threshold of pain and breached the second ring he stopped so I might get used to the intruding digit.
Bobby withdrew his middle digit again and began the process of penetrating my pucker one more time. I was near exhaustion moaning with desire. I was growing tired of delay I wanted him to finger fuck me in earnest -- finish me off. Without knowing it Bobby's finger was deep inside my rectal cavity. His long middle finger found the magical button inside and began massaging it. Oh God, I wanted to cum, scream and shit all at the same time; it felt so fucking good as his finger tip rubbed against my prostate.
With his finger buried deep inside me Bobby returned to orally pleasuring me. I didn't know how much longer I could hold out or if I wanted to. My mentor's mouth had fully engulfed my cock and was bobbing up and down on it as his finger continued exploring my anal cavity. I was screaming out for him to fuck me and suck me. I yelled at the top of my lungs that I wanted him buried deeper in me and to suck me forever. When I blew my load I almost suffocated Bobby with the powerful amount of spooge I blew down his throat. He started gagging and had pull off me to spit some of it out before returning to me.
Bobby refused to withdraw his finger from my ass or let my cock go from the grips of his lips. He was draining every ounce of seminal fluid from my nuts. I had just experienced the most explosive orgasm of my young life. I was soaked in sweat and panting to the point of hyperventilating. My eyes were flashing with lightening. I was experiencing dizziness, chest pains and tingling in my hands and feet. My cock was numb and my balls ached.
I collapsed in a state of total exhaustion. I had no more to offer. I couldn't even reciprocate and finish Bobby off. My nerdy mentor turned around on the bed and lay next to me. Smiling at me he whispered in my ear how much he had enjoyed doing me. He told me that after we rested he wanted me to fill him with my cock, fucking him into oblivion. We fell asleep holding each other. From that first time we refined our sexual repertoire, fucking and sucking each other with wanton desire; however, nothing would ever equal that first time being digitally diddled and sucked off by my friend Bobby.